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See all 172 Properties in Cheshire
Harbour House Inn

Harbour House Inn

725 North State Road, Cheshire
    3.5 out of 5.0
     
     

    Situated in the mountains, this bed & breakfast is within 6 mi (10 km) of Topia Arts Center, East Hoosac Quaker Meetinghouse, and Susan B. Anthony Birthplace ...

    Harbour House Inn$177

    Harbour House Inn$177
    Berkshire Plaza Hotel

    Berkshire Plaza Hotel

    1 West St, Pittsfield
      3.5 out of 5.0
       
       

      Located in the heart of Pittsfield, this spa hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

      Berkshire Plaza Hotel$91

      Berkshire Plaza Hotel$91
      Vacation Village in the Berkshires

      Vacation Village in the Berkshires

      276 Brodie Mountain Rd, Hancock
        3.0 out of 5.0
         
         

        Situated in Hancock, this condo building is within 9 mi (15 km) of Mount Greylock State Reservation Visitor Center, Pittsfield State Forest, and Waubeeka Golf ...

        Vacation Village in the Berkshires$131

        Vacation Village in the Berkshires$131
        Yankee Inn

        Yankee Inn

        461 Pittsfield Rd, Lenox
          2.5 out of 5.0
           
           

          Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

          Yankee Inn$76

          Yankee Inn$76
          Jiminy Peak Mountain Resort

          Jiminy Peak Mountain Resort

          37 Corey Rd, Hancock
            3.0 out of 5.0
             
             

            Located in the mountains, this Hancock condo resort offers ski-in/ski-out access within 12 mi (20 km) of Mount Greylock State Reservation Visitor Center, Waubeeka ...

            Jiminy Peak Mountain Resort$115

            Jiminy Peak Mountain Resort$115
            Berkshire Hills Country Inn

            Berkshire Hills Country Inn

            1146 Cold Spring Road, Williamstown
              2.5 out of 5.0
               
               

              Situated in Williamstown, this hotel is within 3 mi (5 km) of Williamstown Historical Museum, Waubeeka Golf Links, and 62 Center for Theater and Dance. Chapin ...

              Berkshire Hills Country Inn$69

              Berkshire Hills Country Inn$69
              The Orchards Hotel

              The Orchards Hotel

              222 Adams Rd, Williamstown
                3.5 out of 5.0
                 
                 

                Situated in a rural location, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin Library of Rare Books and Manuscripts. ...

                The Orchards Hotel$127

                The Orchards Hotel$127
                Hilton Garden Inn Lenox Pittsfield

                Hilton Garden Inn Lenox Pittsfield

                1032 South Street, Pittsfield
                  3.0 out of 5.0
                   
                   

                  Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

                  Hilton Garden Inn Lenox Pittsfield$110

                  Hilton Garden Inn Lenox Pittsfield$110
                  Hampton Inn & Suites Berkshires Lenox

                  Hampton Inn & Suites Berkshires Lenox

                  445 Pittsfield Rd, Lenox
                    2.5 out of 5.0
                     
                     

                    Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary ...

                    Hampton Inn & Suites Berkshires Lenox$112

                    Hampton Inn & Suites Berkshires Lenox$112
                    Berkshire Mountain Lodge

                    Berkshire Mountain Lodge

                    8 Dan Fox Dr, Pittsfield
                      3.0 out of 5.0
                       
                       

                      Situated in Pittsfield, this lodge is 1 mi (1.7 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

                      Berkshire Mountain Lodge$116

                      Berkshire Mountain Lodge$116

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